Epetirimod → 6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine

HRID 497755ノート

反応式

HRID 497755 の反応式
[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[H][H]>FC(F)(F)C(O)=O.[Pt]=O>[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1

参加物

5

反応物 2

HCID 9942845EpetirimodHCID 178418361HCID 178418361、化合物

生成物 1

HCID 221726996,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 6422Trifluoroacetic acid溶媒

実験手順

A catalytic amount of platinum oxide was added to a solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (0.46 g) in trifluoroacetic acid (10 mL). The reaction mixture was reduced on a Parr apparatus under 45 psi (3.15 Kg/cm2) hydrogen pressure for 4 hours. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated under vacuum. The residue was combined with aqueous sodium bicarbonate then a small amount of 10% sodium hydroxide was added. The resulting precipitate was extracted with dichloromethane. The dichloromethane extract was dried over magnesium sulfate then concentrated under vacuum. The residue was purified by flash chromatography (silica gel eluting with 5% methanol in dichloromethane containing 0.5% ammonium hydroxide). The eluant was concentrated under vacuum. The residue was recrystallized from ethyl acetate to provide 6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a solid, m.p. 222-226° C. Analysis: Calculated for C13H19N5: %C, 63.65; %H, 7.81; %N, 28.55; Found: %C, 63.07; %H, 7.51; %N, 28.00.

後処理

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under vacuum
  4. additiona small amount of 10% sodium hydroxide was added
  5. extractionThe resulting precipitate was extracted with dichloromethane
  6. extractionThe dichloromethane extract
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationthen concentrated under vacuum
  9. customThe residue was purified by flash chromatography (silica gel eluting with 5% methanol in dichloromethane containing 0.5% ammonium hydroxide)
  10. concentrationThe eluant was concentrated under vacuum
  11. customThe residue was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-0285a9010c1c41deb2330506ac94428a
出典データセット
uspto-grants-2005_09
特許番号
US06949646B2

反応ノート

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